Chief of Staff

About Freight Hero FreightHero is an AI-native services company built to support the freight brokerage industry, which is in dire need of it. Robin, our autonomous AI agent, handles back-office work end to end. Our Heroes, a sharp human-in-the-loop team, catch the edge cases. Brokers pay us per load, see ROI in weeks, and reassign or eliminate the teams they used to rent. We are backed by incredible investors, Dynamo Ventures, AI Fund, Field Ventures, Flybridge Capital and other major names in VC. The thesis is proven. What is next is growth, and that means building a team of incredible people around us to push the company to the next level. The product is real, the customers are real, the revenue is real, and joining now means shaping how this company runs. About the Role This is one of the most cross-functional seats in the company. As Chief of Staff, you will work directly with the CEO to run the business. You will own the operational backbone that keeps everything else moving, including project management across functions, people operations, basic accounting and finance alongside our external partner, and the kickoff of our marketing, brand, and social media efforts. You will not be walking into an established playbook. You will be building it, and you will be doing it across a wide surface area. This is the right seat for someone who wants to see how a venture-backed company is built from the inside, who is energized by ambiguity, and who can move between strategic synthesis and operational detail without losing momentum. The role rewards judgment and bandwidth more than functional depth in any single area. You will get exposure to every part of the business and meaningful ownership from day one. As individual functions mature, parts of your scope will spin out into dedicated roles. Marketing in particular will eventually become its own function, and you will have helped lay the foundation for it. About the Role This is a founding role and one of the most cross-functional seats in the company. As Chief of Staff, you will work directly with the CEO to run the business. You will own the operational backbone that keeps everything else moving, including project management across functions, people operations, basic accounting and finance alongside our external partner, and the kickoff of our marketing, brand, and social media efforts. You will not be walking into an established playbook. You will be building it, and you will be doing it across a wide surface area. This is the right seat for someone who wants to see how a venture-backed company is built from the inside, who is energized by ambiguity, and who can move between strategic synthesis and operational detail without losing momentum. The role rewards judgment and bandwidth more than functional depth in any single area. You will get exposure to every part of the business and meaningful ownership from day one. As individual functions mature, parts of your scope will spin out into dedicated roles. Marketing in particular will eventually become its own function, and you will have helped lay the foundation for it. What Success Looks Like A high-functioning Chief of Staff at FreightHero looks like this: The business runs on cadence. Leadership meetings, cross-functional reviews, and operating rhythms are well-defined and consistently executed. Cross-functional projects move forward without the CEO in the loop on every detail. You unblock, you escape when needed, you close the loop. People operations is structured and reliable. Hiring funnels, onboarding, and basic HR workflows run smoothly without friction. Finance and accounting basics are handled cleanly. Bills are paid, books are reconciled in coordination with our external accounting partner, and the CEO has the financial visibility needed to make decisions. Brand, marketing, and social media efforts are off the ground. There is a coherent brand voice, a presence in the market, and the foundations of a content and demand engine that a future marketing hire can take over and scale. Your job is to make all five of those things true. Key Responsibilities Run-the-Business Operations Own the operating cadence of the company: leadership meetings, cross-functional reviews, business reviews, and the rhythms that keep the team aligned. Coordinate and execute strategic cross-functional initiatives on behalf of the CEO. Identify operational gaps, design lightweight processes to address them, and implement without overengineering. Maintain the playbooks, documents, and tooling that make the company easy to run as it scales. People Operations Own the hiring funnel end to end: scheduling, candidate communications, interview coordination, and offer administration. Run onboarding for new hires across functions, ensuring everyone lands well in their first weeks. Maintain basic people ops infrastructure: HR tooling, employee documentation, and the policies that keep us compliant and organized. Support the CEO on culture and team-building initiatives as the company grows. Finance and Accounting (RTB) Own the day-to-day financial operations of the business in coordination with our external accounting partner. Manage AP/AR, expense reporting, vendor payments, and the basic financial workflows of the company. Keep the books clean and the CEO informed on cash position, burn, and key financial signals. Coordinate with part-time finance and analytics support as those functions are stood up. Marketing, Brand, and Social Media (Kickoff) Stand up the foundations of FreightHero's marketing, brand, and social media efforts. This is greenfield. You will be defining the voice, the channels, and the cadence. Manage marketing tooling and infrastructure (CRM, marketing automation, social media platforms). Familiarity with tools like Apollo, HubSpot, or similar is a plus. Drive content production across LinkedIn, the company blog, and other channels, working with the CEO and external collaborators as needed. Lay the groundwork that a future dedicated marketing hire will inherit and scale. AI-Forward Ways of Working Use AI tools and AI Agents actively in your day to day, from drafting communications and synthesizing meeting notes to building dashboards, automating routine workflows, and scaling your own output. Partner closely with the AI Deployment Accelerator (a peer in the CEO Office) to identify and deploy internal AI agents that automate parts of your scope. Continuously look for ways to use AI to do your job faster, more accurately, and at greater scale. What We Are Looking For 4 to 6 years of experience, ideally a combination of structured early career (consulting, investment banking, banking, or similar) and time in a high-growth startup or other generalist-friendly operating role. Post-MBA candidates wanting to break into the venture or startup ecosystem are encouraged, as are operators with equivalent experience Strong execution chops. You ship. You close loops. You move things across the finish line without needing to be reminded. Comfortable across functions. You can move between people ops in the morning, a brand strategy conversation at lunch, and a basic financial reconciliation in the afternoon, and not lose your stride. Strong organizational and project management skills. You manage many workstreams in parallel and nothing slips. Excellent written and verbal communicator. You can write a polished CEO-voice update one moment and a clean SOP the next. High EQ. You build trust quickly across the team and externally, and you handle sensitive information with discretion. Familiarity with CRM and marketing tooling (Apollo, HubSpot, Salesforce, or similar). Not a hard requirement, but a meaningful plus given the marketing kickoff scope. Genuinely curious about AI and technology. You do not need to be technical, but you need to lean in, learn fast, and find ways to use new tools to do your job better. Comfortable operating in an environment with ambiguity and rapid change. You see ambiguity as opportunity, not friction. Why Freight Hero Work directly with an experienced, previously exited founder building one of the most cross-functional roles at the company. Get in on the ground level of a venture-backed startup with strong PMF signal and real customer traction. Real ownership across a wide surface area. You will touch nearly every part of the business in your first year. A clear path forward as the company scales, whether that is into a leadership role within one of the functions you helped build, or into a more senior strategic seat alongside the CEO. A front-row seat to AI and logistics, two of the most consequential spaces in B2B tech right now. Competitive salary and equity in a venture-backed company with significant upside. #J-18808-Ljbffr